The Writer, the Girl With Red Lipstick, and the Musician
by lulamae-golightly
Summary: Daria Morgendorffer, a young writer, moves to New York in 1963 and meets an artist and a musician. (trying to pick up this story again after a long hiatus)
1. Chapter 1

**A/N: This is an attempt I thought would be interesting. Daria belongs to MTV.**

_Manhattan, New York_

_September 1963_

A young woman hugged her arms closer to her body as a wind passed by, blowing her hair into her face. She stared up at the tall building that she knew now as her apartment building. It was a rusty red color, made of brick. Not the most high end place you could end up. But it was cheap, and it was decent. A girl stood on a balcony, smoking and looking down. She waved and received one in return.

Once she had gotten her keys, she took a long, tedious flight of stairs to floor eleven of twenty. The girl with the cigarette was just walking out, and they collided. "Oh!"

"S-sorry,"

"No problem," she was taken aback by the girl's features. She had bright blue eyes, high cheekbones, and wore red lipstick. "I was just going down to welcome you."

"Oh," was all she got in reply.

"That sounds kinda weird, I know. But no one _interesting_ lives here! No one _young."_

"I'm young..."

"I am too." the girl brushed her short, raven hair out of her eyes. "I'm Jane Lane. Probably should've mentioned that earlier."

"Daria Morgendorffer," they shook hands. Jane had a strong grip. Her fingernails were crimson. She wore a white t-shirt with no bra and torn jeans that went to her ankles. This was quite the contrast to Daria's beige jacket and black skirt. Their features were also very different; Daria wore no makeup except for a light pink on her lips. She had brown eyes, and she wore large glasses.

"So your room is gonna be on this floor?"

"Indeed," Daria nodded. "I didn't think I'd meet my neighbors so soon, though."

"Come in and meet another one," Jane invited her into her apartment. She seemed like a nice enough girl, so Daria accepted. Jane was different. Daria liked it.

The girl's apartment was an explosion of color, paintings, and other various things lying around. "I paint," she explained.

"I see that."

"It's fun, but it's not the easiest business. I'm trying my hardest, though."

"Janey," a deep, male voice called out. A boy in a t-shirt and torn jeans much like Jane appeared. He had shaggy black hair and some facial stubble. "Who's this?"

"Trent, this is Daria Morgendorffer. She just moved in and I'm trying to make her feel welcome. Daria, this is my older brother Trent."

"Hey," Trent nodded in Daria's direction. She returned the nod. "So you're new?" he asked, joining the two on the couch. Trent looked very much like his sister, with the same light blue eyes and full mouth. He caught Daria looking at him and half smiled as she blushed and looked away.

"Yeah, I came from Lawndale, California."

"California. Fancy." Jane commented.

"Nothing special, really. Not in Lawndale."

"What brings you to New York?" Trent asked, a question that Daria did not know the answer to yet.

"I...I'm not sure. I wanna write...be a journalist, and I thought I might have...more of a chance here, I guess."

"I've lived here for about six months. Came when I turned nineteen and never looked back. Anything's better than the hellhole of Texas."

"And your brother came too?"

"Yup," Trent replied. "And I don't regret it. How old are you?"

"I just turned twenty."

"Same here, my birthday was in June." Jane replied. "So, Daria, what do you like?"

"What do I like? What do you mean?" _I like a lot of things,_ Daria thought. _I like...I like coffee...and cigarettes...I like the rain...I like the sound of my typewriter...I like Jane's red lipstick and I like her brother's hair and his eyes...I like how he smells like freshly washed clothes...I like words..._

"Oh, you know," Jane said, leaving it at that.

"I like writing and...coffee." Trent chuckled, and a pink spread across Daria's cheeks again.

"I like paint and cigarettes. That works out." Jane smirked a red lipstick smirk.

"Janey, we should let her get unpacked and settled," Trent said.

"Oh, yeah. Daria, do you need any help? Trent can..."

"U-um, er...well..." she began to stumble over her words.

"I'll definitely help," he agreed. She and him walked across the hall to her apartment, bringing her few bags along. "Not a lot of stuff," he said.

"I guess," Daria shrugged. "What do you do?"

"I play guitar in a band," he replied, "and sing." The apartment was small, with one bedroom, a bathroom, a kitchen and living room. The bedroom had only a small cot, dresser, and desk. They began unloading her bags, starting with her clothes, which she put in the dresser. "Whoa," Trent breathed, taking her typewriter out of a bag. It was one of her most prized possessions. "This is pretty cool."

"Yeah, my mom gave it to me on my eighteenth birthday," she said, setting it carefully on her desk. They unpacked the rest of her things, mostly in silence, until they were done. "Thanks for helping me, Trent. And tell your sister thanks for being so welcoming. Once I have things set up, you guys can come over for dinner some night, I promise."

"Anytime, Daria," he squeezed her shoulder. "By the way," he added on his way out the door, "I like your glasses."

Why he said it, she was unsure, but it made her chuckle. She immediately sat down in front of her typewriter, lighting a cigarette and placing her fingers to the keys that were so familiar to her. At the top of the page, she wrote:

_The Girl With Red Lipstick_

_(and her brother)_


	2. Chapter 2

**A/N: Thanks for the follows and reviews already, I really appreciate it! A quick note, though: I don't condone smoking at all! However, it was _very_ popular in the 1960's...and just about every decade before that. But yeah, smoking is a really bad habit—don't smoke. :P**

After almost a week, Daria was settled and was starting to get used to her new apartment. She got to know Jane and Trent more after having dinner with them. She learned their mother and father often left them alone to go off on their own journeys. Trent practically raised his little sister. Jane had always liked to paint, and she also loved to run. "It clears my mind," she said. Trent formed his rock band, The Spirals, when he first moved to New York. They played frequently at a little club in the city.

Trent and Jane learned Daria was always an outcast in high school, especially compared to her younger sister Cecily, who now went by her middle name Quinn. She was in her first year of college. "Why didn't you go?" Jane asked.

"I went for about a year, at a community college, but I didn't really get a lot out of it," Daria confessed.

"I didn't go at all, so don't feel bad," Jane replied. "Where does your sister go to college?"

"Pepperhill. Still in California."

"That's a party school," Trent said.

"I know," Daria sighed. "But all her little friends went there, too, so she just _had _to. The thing is, Quinn is smart! She's very smart and could totally get a great education and go onto great things, but she chooses to go to a party school. And when I tell her that it's a bad decision, she tells me, "Well it's better than going to no college at all,"." She shook her head. "Sorry, I rambled."

"No problem," Trent assured her. "We like listening to you." The damn blush flooded her cheeks again. Out of the corner of her eye, she saw Jane smirk at her. "Speaking of listening," Trent began, "The Spirals have a gig tomorrow. Why don't you come? I'll get you guys in free."

"Oh, that would be great, but I can pay-" Daria began.

"No, really. I've always gotten Janey in free, I can definitely let you in. Besides, you're her friend, and she's always had a good taste in friends."

"I've barely _had _any friends," Jane scoffed.

"Well, I like Daria." Trent concluded. "Will you come?"

"Sure," Daria agreed.

* * *

_He asked me to come to his band's performance with Jane tomorrow night, which sounds wonderful, I'm just nervous. I've already been a blushing idiot around him, he _must_ know how I feel. But there really isn't any harm in going. Maybe his band is good._

To Daria surprise, the band was...mediocre. She had heard worse. But she had _definitely _heard better. Trent had a very nice voice, however. She had never had any musical talent, but she could tell he was good, but the band was...decent.

After a few songs, Trent joined her and Jane in a booth in the corner of the club. "Hey, guys," he said. "Lookin' good, Daria," he commented. Daria had tried to look nice by wearing a casual green dress and flat black shoes.

"Thanks," she replied.

"Trent!" a voice called from across the room. A girl with long, red hair and big brown eyes crossed over to them. Trent got up from his seat and kissed her cheek.

"Didn't know you were coming tonight," he said. "It's nice to see you."

"I come to all your gigs," she said, laughing as they embraced. "Hey, Jane."

"Hey Robin."

"Daria, this is my girlfriend Robin." Trent introduced her. _Girlfriend?_ "We met here when I was just starting out. Robin, this is Daria. She just moved in, from California."

"Nice to meet ya," They shook hands awkwardly. Daria felt overdressed after seeing Robin in a cleavage-showing t-shirt and beige pants. She had a smattering of freckles across her nose and cheeks. It reminded Daria of her sister.

"Daria's pretty groovy, if I do say so myself." Trent said.

"I guess," the two slid back into the booth next to Jane.

"Want a drink?" Robin asked.

"Sure," Trent agreed. "Beer for me. Janey?"

"Just a coke,"

"I'll have the same," Daria added.

"Gotcha. Back in flash," Robin left to order their drinks.

"I didn't know you had a girlfriend," Daria said._ We've talked so much in the past week I think you should've mentioned it at least once._ She thought of adding, but that was a little too snappy. _I shouldn't even be mad—it's not like he liked me or anything..._

"Yeah, I probably should've mentioned that. But she's really great, you two will get along."

Robin soon game back with their drinks. "So, Daria, what do you do?"

"I write."

"Ah...a novelist."

"Journalist," Jane corrected.

"Ah." Robin repeated uneasily. "How are you, Janey?"

"Good, for the most part." A slow song that Daria had heard over the radio (and hated), began to play.

"Ooh, this is a good song." Trent said. "Dance with me, Robin?"

"Always," Robin smiled and they made their way to the dancefloor. Daria was silent, brow furrowed as she sipped her coke.

"Something's wrong." Jane noticed.

"No," she replied.

Her friend sighed. "I may not have known you for very long, Daria, but I know when you're lying to me. This is about Trent, isn't it?"

"I don't care about Trent."

"I know how much you like my brother."

"Can we please...not talk about this?"

"Daria," Jane began.

"No more, please."

"Well...okay."

"Look..." Daria sighed. Her head was pounding. It smelled too much like smoke, which didn't usually bother her, but now it was irritating her and gave her a headache. Everything was too loud and too confusing. "I need to go home. I'm tired and I have a lot on my mind. I'll take a cab home." she began to gather up her belongings.

"No, Daria!" Jane exclaimed.

"Really, Jane. I'm tired. See ya tomorrow." Realizing it was a lost cause to convince her to stay, Jane simply sighed and let her go. "Tell Trent I said bye."

As soon as she got home, she sat down at her typewriter.

_Thoughts From A Young Woman Who is Mad at Herself_

_I've never been good with titles—I just need to let off some steam._

_I shouldn't really be so mad at him, because he doesn't know how I feel. Well, I think he doesn't. I wouldn't be surprised if he did, considering that I'm a total fool around him. And his girlfriend is so pretty, redhead and skinny and tall. I was the mousy one in high school, I always will be, I suppose. My only friends have been words, and when I met Jane and Trent I was glad to have someone. They're still my friends, I'm just being stupid because I'm head over heels for Trent. I sound so dumb. I need to sleep. I need to stop thinking._

_-DM_

**A/N: Thanks again for the reviews and follows, I'm glad I'm getting support so early in this story!**

**-Lulamae**


	3. Chapter 3

After the incident with Robin and Trent in the club, Daria began to submerse herself in writing and submitting to magazines. Not personal stuff; more cynical pieces about society, fashion, people...et cetera. Within a week, one was published in a magazine for aspiring writers called _Billings. _It was very well accepted.

"I'm happy for you, you know that?" Jane asked as they walked along the streets of New York, window shopping.

"Thanks," Daria replied. She couldn't help it—she was glad, too. She had spent nearly a month now in New York and was already published; perhaps she was onto something. "Really, though, that article was nothing special. But that dress is..." she stared longingly at a light yellow dress with sunflowers on it. She had never been big on fashion or clothes or what have you, but she knew a fine article of clothing when she saw it. However, she also knew an_ expensive _article of clothing when she saw it.

"You said just the other day you didn't wear yellow," Jane said.

"I do if it looks like that. Remind me to put that on my 'saving up for' list."

"I didn't know you _had _a 'saving up for' list."

"I didn't either, until now." Jane chuckled and they walked on. A display in a shop across the street caught Daria's attention, causing her to run into someone.

"Oh, I'm sorry!" she exclaimed. _What is it with me running into people?_

"No worries," it was a man, with clean cut brown hair and green eyes. He gave her a smile.

"I wasn't looking...I'm really sorry..."

"Again, you're fine. What brings you out to the city this fine day?"

"Oh, just window shopping," she looked at her feet uneasily. He was handsome. Not in a different, not traditional Trent Lane way. In a classic way. "Trying to find...inspiration."

"Inspiration? Are you an artist?"

"Of sorts, I guess. I'm a writer." The boy cracked another smile.

"That's great," he replied. "Novelist? Journalist?"

"Sort of a journalist. I've only been published once...and it was in _Billings._" she admitted.

"I'm an editor for _Billings!_" he exclaimed.

Daria looked up. "Really. You're kidding."

"Nope!"

A grin began making its way onto her face. "I wrote _The Downsides to Following Trends_."

"Oh, everyone was just _gushing_ about how clever it was! And from someone so young! See, I help edit the articles column, so I get to read all of them, and your was one of my favorites. Daria...Morgendorffer, was it? My name is Thomas Sloane." They shook hands, smiling.

"Yes, and this is my friend Jane Lane." they shook hands and exchanged greetings.

"Now, I hope this doesn't sound too...quick, but could we have coffee tomorrow afternoon? I'd love to talk to you more." Thomas asked.

"Of course! Where at?" They agreed on a tiny coffee shop by the _Billings _building at one in the afternoon.

"I look forward to seeing you!" Thomas said as he walked off. Daria smiled and waved goodbye at him.

"Damn," Jane sighed. "You've only been here for a month and you're picking up boys."

"He's an editor of a magazine, Jane! God, I wish I had that sunflower dress..."

"So you've completely forgotten about my brother at this point?" Daria's nose wrinkled in annoyance.

"Your brother is my friend," she replied. "That's good enough for me."

"Really?"

"Really." Jane had found that questioning Daria only made her more annoyed, so she shrugged and continued on.

* * *

The next day, Daria appeared in Jane's apartment wearing a brown, form-fitting dress, loafers, and her hair up. "Do I look alright? Am I overdressed?"

"You look great. Thomas is gonna love it." Trent walked in, searching the fridge for food. He looked at Daria quizzically.

"What's the occasion?" he asked.

"She's got a date," Jane smiled. "With the _editor _of a _magazine._"

"Interesting," Trent said, seemingly uninterested. "Have we got any milk left?"

"I drank the rest of it," Jane admitted.

"Damn," Trent groaned. "I've got band practice tomorrow and I'm so tired of hearing Nick and Max fight all the time. We barely get anything done."

His sister shook her head. "You all get on each other's nerves too much."

Daria checked her watch. "I have to go now. I'll talk to you later,"

"You better!" Jane exclaimed as Daria checked herself one last time in the mirror.

"You're sure I look okay?"

"You look _fine._ Go have fun."

"Who's this guy she's going out with?" Trent asked once she had left.

"His name is Thomas. He's the editor of that writing magazine, _Billings._ Daria bumped into him yesterday, they struck up a conversation and the next thing ya know he's asking her out."

"Hmmm," he replied.

"He seemed nice enough, and Daria was so happy. Why do you care about all of this?"

"I care about Daria!"

"Sure, why didn't you tell her you had a girlfriend then?"

Trent looked at his sister slack-jawed for a moment, his eyebrows furrowed confusedly. "Why...why does that matter?"

"Because you led her on!"

"I didn't lead her on!"

"Well it certainly seemed like you were trying to start something! You _did _lead her on, Trent. Admit it."

"Only because...me and Robin had a fight that week, remember? And she was new and pretty and..." Everything was coming out wrong.

Jane made a noise of disgust. "Oh, so you just flirt with every girl who's new and pretty! Sometimes you can be such a jerk." She stormed off to her room, slamming the door for emphasis. The two didn't have fights very often, but when they did it made them both sad, though neither would admit to it.

* * *

The coffee shop was teeming with people and smoke, but it was somewhat comforting to Daria nevertheless. Thomas arrived shortly after her, and they took a spot in a table by a window where the sun streamed through. "You look very nice," Thomas told her, lighting a cigarette. He offered her one, and she accepted. "Thank you for agreeing to this, especially with it all being so sudden, I just wanted to get to know you. You're a wonderful writer."

Daria gave her usual Mona Lisa smile. "Thank you."

They ordered some coffee and light snacks, and they chatted easily about anything and everything for a bit. Writing, books, family. She learned Thomas had lived in New York since he was two. The Sloanes were old money, but he was the only one who had no interest in going into his father's business. His story was a lot more colorful and detailed in comparison to her little explanation of her normal teenage years, but he listened anyway.

* * *

After their lunch, they strolled around the city for awhile. "Are you working on anything more, writing-wise?" he asked.

"I want to start a mystery novel," Daria admitted.

"Hmmm, a mystery. That's old fashioned."

"I like old fashioned things," she retorted.

Thomas raised an eyebrow quizzically. "Well, I do look forward to reading it." They spent another hour chatting and walking. She was enjoying getting to know him, despite little flaws that she knew if this was to go anywhere, she would have to accept.

They stood in front of the coffee house to say goodbye. "I've really liked talking to you, Daria," Thomas told her. He leaned down and pecked her cheek. Daria stood on her toes and kissed his lips, in front of the coffee shop and everyone. She had kissed a few boys before, but it was usually in a private place like behind the bleachers or his backyard. She felt a little odd, but the kiss, short but sweet, was nice. Maybe this _was _going somewhere.

"Goodbye, Thomas." she smiled her quiet smile, and he smiled back.

"Tom," he corrected. "See you soon." she hailed a cab, and he watched her disappear.

* * *

When Daria arrived back at her apartment building, she immediately knocked on Jane's door. Trent answered. "Hey, Daria," he mumbled, sounding rather disheartened, and looking it as well.

"Hi," she replied uneasily. "Is Jane here?"

"She's in her room," he explained, letting Daria in. "Janey!"

"Fuck off, Trent!" Jane called back. Daria's eyes widened.

"Um," she began.

He sighed, "It's a long story. How was the date?"

"It was all right," Jane burst out of her room.

"Daria! You didn't tell me you were here."

"I tried to!" Trent exclaimed. Jane rolled her eyes.

"How was the date?" she asked, disregarding her brother. The two settled themselves down on the loveseats as Daria described the date; what they talked about, the food, a little bit about Tom. As she spoke, she saw Trent was listening warily in the kitchen, pretending not to. "Did he kiss you?" Jane asked, a mischievous smirk spreading across her face.

"Sort of," Daria replied, "He kissed my forehead, then I-" her friend gasped.

"Daria, what did you do?!"

"God, let me finish! I kissed his...his lips." Jane laughed.

"Aw!" the bespectacled girl shook her head.

"I'm twenty, does it come as that much of a surprise I can kiss a boy?"

"But it was so sudden! So serious so fast! You barely know the man!"

"You're so dramatic, Janey," Trent said from the kitchen. She shot him a dirty look. "But she does have a point, Daria. It _was _your first date with him."

"Why do you care about it, Trent?" Daria asked, a little ruder than she meant to sound.

"Because you're my sister's friend. And mine. And I want you to be safe." She bit her lip and blushed, trying to cover it with her palm.

"That's real heartfelt, Trent, but I think Daria's gonna be okay. Though I still think it was a teensy bit rushed. I just didn't expect it out of you."

Daria took her glasses off and cleaned them on her shirt. "Hey, I'm looking forward to seeing where it goes, personally. I really like the guy, and he must like me, too. After all, your brother said I was 'pretty groovy'." Trent chuckled and she stifled a smile.


	4. Chapter 4

Life in New York became routine, but a wonderful routine. Daria wrote more, and got very good reception. She also went on quite few more dates with Thomas, and even took him to see the Spirals at the little club. It seemed like an odd place for someone as refined as Thomas to be in, but he was somewhat impressed. Jane was skeptical when she saw them together, as a couple, but at the end of the night she pulled Daria aside and voiced her approval. Trent spent most of his time dancing with Robin when not onstage, and otherwise was indifferent. Though things between Jane and Trent had cooled down; they always made up fairly quickly after fights.

"It's because we don't have anyone else. I mean, Trent's got his band boys and I've got you but...it's a sibling thing." Jane explained. Daria understood.

One night, Daria and Thomas were taking a walk back to his apartment (which she still hadn't seen yet), he laced her fingers with his. It wasn't the first time he had done that, but now it made her wonder. "Thomas?"

"Tom. Yes?"

"Are we...um...together?"

Tom raised an eyebrow. "Together?"

"Like...are we in a committed romantic relationship?" she wished she could speak better around him, that she could word things like she could on paper.

He chuckled and squeezed her hand a little. "Do you...want to be?"

"Do you?"

They stopped walking. "Don't answer my question with a question."

"Well...I do," she replied honestly. "But...do _you_?"

He smiled, running his fingers through her hair briefly. "I do. I like you very much, Daria." She blushed, looking down at her (well, _their_, they were standing so close together) feet. They both wore brown loafers.

"We match," she said quietly. He gave her a confused look. "Our shoes."

He acknowledged them, briefly, then looked back up into her eyes. "So...what does that mean?"

"It doesn't mean anything, I just think it's funny we have matching-"

"No, not about our shoes. About...us. What does it mean, what we said?"

"I...I want this. I want...us." As she spoke, an uneasiness filled her stomach as if she wasn't completely sure. She brought her hand to her mouth, chewing her nails, an awful habit that her mother was constantly on her back about. Tom gently pulled her hand away, kissing her lips. It was a long, breathless kiss, and when they pulled apart, Daria let go of a breath she felt she had been holding in forever. "I'm a little tired," she admitted when they got there. "I think I'm going to go home."

"Oh, well, alright," he replied. "I'll talk to you soon." They shared another kiss and said goodbye.

They walked the rest of the way in silence, and Daria took a cab home, her thoughts a tangled web of confusion. She liked Tom. She liked talking to him-he was intelligent and they had very good discussions. She liked that he liked her writing, and that he gave her very good constructive criticism. She liked that they had the same taste in several things. She liked kissing him, and she liked his appearance, and she just..._liked him._ She knew that. And yet she didn't know if she really did want this. She didn't know if it would last, if it would go anywhere. She didn't know how anyone would react to it. She didn't know a lot. That didn't bother her usually, she liked learning new things. But this was too much.

Once she got home, she stepped into the elevator, running into Trent. "Hey," he said.

"What happened?" He looked very tired. (More than usual.)

He groaned, rubbing his eyes. "Breaking up with Robin."

"Oh," Daria replied quietly.

"What's going on with you?"

"Tom's my steady now." _God, I hate that word. _Steady sounded so...high school.

Trent looked surprised. "That's...great."

"Yeah, I'm not so sure myself."

"Don't you..want to be with him?"

She chewed her lip, and even though the elevator door opened, they stayed inside it. "I do. But...I guess I'm thinking too much and things moved a bit fast."

"It's up to you, Daria, but...be happy, okay? You really deserve it." He leaned down and gave her a quick embrace, then waved and walked into his apartment. Daria sighed and walked into hers. She was welcomed by quiet, by the familiar coolness her apartment had. She slipped into pajamas then crawled into bed, but didn't fall asleep for several more hours.

_Goddammit Morgendorffer, do you always have to _think _so much?_

**A/N: I don't like fics that use the "evil" Tom thing. Tom was a good character, I think, and it was obvious him and Daria were not perfect for each other-they were in high school, relationships don't usually last and especially since it was Daria's first, things weren't going to end perfectly. I like to think they'd remain friends, and I'm just trying to figure out where this fic is going, really. Sorry if I'm upsetting anyone by putting them together. But things will change.**

**-Lulamae **


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